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Questions about work and career
9 hand-curated question banks on work and career, each tailored to a specific relationship. What you ask your mom isn't what you ask your best friend.
A few questions from these sets
- Best friend You had a line you gave people back then when they asked about your future — was that the true answer or the presentable one?
- Coworker What almost became your career instead?
- Dad Who was the best boss you ever had — and what made them good?
- Grandma When you say you 'didn't work,' what were you actually doing all day?
- Grandpa What was your job during the war or your service years — what were you actually doing?
- Mom What's a job or promotion you turned down, and why?
- Partner When you've had a brutal day, what do you actually need from me when you walk in — and am I getting it right?
- Sibling Growing up, who did the family expect more from when it came to work — and how did that land on you?
- Son What counts as a mistake in your field that only somebody inside it would recognise as one?
- Best friend
50 Questions to Ask Your Best Friend About Work and Career
50 questions only a best friend can ask about work: the plan she told you first, what she stopped mentioning, and what the job has cost the two of you.
- Coworker
32 Questions to Ask a Coworker About Their Work and Career
32 career-story questions colleagues never ask each other — how they got here, the job that taught them most, what they'd tell their younger self.
- Dad
50 Questions to Ask Your Dad About Work and His Career
50 questions to ask your dad about work and career — first jobs, bosses, what being the provider meant, and what he'd tell his younger self.
- Grandma
30 Questions to Ask Your Grandma About Her Work and Career
30 hand-curated questions about your grandma's working life — the narrow options open to women of her era, and the farm and home work that never counted.
- Grandpa
30 Questions to Ask Your Grandpa About His Work and Career
30 hand-curated questions about your grandpa's working life — the trade he learned, the war served as work, the job held for life, and the man it made.
- Mom
50 Questions to Ask Your Mom About Her Work and Career
50 hand-curated questions for your mom about her working life — the jobs she held, the trade-offs she made, and the unpaid work of raising you.
- Partner
30 Questions to Ask Your Partner About Work and Career
Thirty questions for the partner you share a life with about their work: the ambition, the stress they carry home, and whether they feel backed by you.
- Sibling
50 Questions to Ask Your Sibling About Work and Career
50 questions for the sibling who started where you did and chose differently — the careers you compare, the rivalry, and what they really think of it.
- Son
50 Questions to Ask Your Son About Work and His Career
50 questions to ask your son about work — for a parent who can no longer judge the field, the money, or the man his colleagues get all week.